Triethylamine → N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Difluoroacetic acid	HCID 9788	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	2-Bromo-4-fluoro-α-methylbenzenemethanamine	HCID 57086919	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide	HCID 57445093	66.3%

Reaction Steps

Add difluoroacetic acid (777 mg, 8.1 mmol) to a mixture of 1-(2-bromo-4-fluorophenyl)ethanamine (1.18 g, 5.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.55 g, 8.1 mmol), 1-hydroxybenzotriazole hydrate (1.24 g, 8.1 mmol), and triethylamine (2.26 mL, 16.2 mmol) in DCM (20 mL) at 0° C. Stir the mixture at RT overnight. Dilute the mixture with DCM, wash with water and aqueous saturated sodium chloride. Separate the organic layer and dry over sodium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography [5% to 50% ethyl acetate in hexanes] to give the title compound (1.06 g, 44%). MS (ES) m/z 296 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08063035B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-f65d95b124214c7fbf1caddf6f6481ca
Source note	uspto-grants-2011_11